IP Library Granted Patent US 10,087,165
Granted Patent B2
US 10,087,165 · App. 15/319,620 · Granted Oct 2, 2018

Fluoroquinolones and use thereof to treat bacterial infections

Inventors: Alexandra Aubry (Massy, FR); Guillaume Anquetin (Massy, FR)
Assignee: Sorbonne Universite
C07D401/10A61K31/496
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Quick Facts
Patent No.
US 10,087,165
App. No.
15/319,620
Granted
Oct 2, 2018
Kind
B2
Abstract

The present invention relates to novel fluoroquinolones, pharmaceutical compositions or medicament containing them and use thereof to treat bacterial infection.

Claims (50)

1. A compound of general Formula I:

and pharmaceutically acceptable salts thereof, wherein:

R 1 represents a saturated or unsaturated, substituted or unsubstituted, branched or unbranched alkyl group comprising 4 to 20 carbons atoms, when the alkyl group is substituted, the substituent is selected in the group comprising halo, hydroxyl, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,

R 2 represents a substituent selected from the group comprising hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,

R 3 , R 4 , R 5 and R 6 may be identical or different and each represents a substituent selected from hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,

R 7 represents a substituent selected from hydrogen, alkyl, alkene, alkyne, cycloalkyl, aryl, halo, hydroxyl, oxo, nitro, amido, carboxy, amino, cyano, alkoxy, haloalkoxy, or haloalkyl,

with the condition that the compounds of formula I are not:

7-(4-butylpiperazin-l-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-heptylpiperazin-l-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

7-(4-butyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-hexyl-3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-(4-hydroxybuty)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

with the condition that when R 2 is a hydrogen and R 7 is a fluorine, R 3 , R 4 , R 5 and R 6 are not a methyl group.

2. The compound according to claim 1 , wherein R 1 represents a saturated or unsaturated, substituted or unsubstituted, branched or unbranched alkyl group comprising 5 to 16 carbons atoms.

3. The compound according to claim 1 , wherein R 2 represents a substituent selected from the group comprising hydrogen, methyl, methoxy, ethoxy, chloro and fluoro.

4. The compound according to claim 1 , wherein R 3 , R 4 , R 5 and R 6 are identical and represent each a hydrogen.

5. The compound according to claim 1 , wherein R 7 representsa hydrogen, NH 2 or fluoro.

6. The compound according to claim 1 , having the general formula II corresponding to the general formula I wherein R 7 is a fluorine:

and pharmaceutically acceptable salts thereof.

7. The compound according to claim 1 , having the general formula III corresponding to compounds of general formula II wherein R 3 , R 4 , R 5 and R 6 are identical and represent a hydrogen atom:

and pharmaceutically acceptable salts thereof.

8. The compound according to claim 1 , selected from the group comprising:

1-cyclopropyl-6-fluoro-4-oxo-7-(4-pentylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-hexylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-octylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-nonylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-7-(4-decylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-4-oxo-7-(4-undecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-7-(4-dodecylpiperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-4-oxo-7-(4-tridecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-4-oxo-7-(4-tetradecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-4-oxo-7-(4-pentadecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-hexadecylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-pentylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-hexylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-heptylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-7-(4-octylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-7-(4-nonylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-7-(4-decylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-undecylpiperazin-1- yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-7-(4-dodecylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-tridecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-tetradecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-(4-pentadecylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid,

1-cyclopropyl-6-fluoro-7-(4-hexadecylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid,

and pharmaceutically acceptable salts thereof.

9. A pharmaceutical composition comprising at least one compound according to claim 1 , or a pharmaceutically acceptable salt, and at least one pharmaceutically acceptable carrier, diluent, excipient and /or adjuvant.

10. The pharmaceutical composition according to claim 9 , further comprising a therapeutic agent and/or active ingredient.

11. A medicament comprising a compound according to claim 1 .

12. The medicament according to claim 11 , further comprising a therapeutic agent and/or active ingredient.

Assignments (2)
CHANGE OF NAME Recorded Aug 7, 2018
From: UNIVERSITÉ PIERRE ET MARIE CURIE - PARIS 6 (UPMC); UNIVERSITÉ PARIS-SORBONNE (PARIS IV)
To: SORBONNE UNIVERSITE
Reel/Frame 046567/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 11, 2017
From: AUBRY, ALEXANDRA; ANQUENTIN, GUILLAUME
To: UNIVERSITÉ PIERRE ET MARIE CURIE
Reel/Frame 040946/0968 →
Priority Claims (1)
EP 14173040 · Jun 18, 2014 · regional
Continuity (1)
Related Publication 20170144992A1 · May 25, 2017